Jon Holmes, a kayak instructor, is one of five men will who attempt to paddle the 465-mile route. If Verlen Kruger was still carving through rough waters, the burly paddling icon probably would not want to miss a new, 465-mile adventure along the Huron and Grand rivers.

“He’d try to go with them,” said Jim Woodruff, a close friend of the late record-setting canoeist who racked up 100,000 water miles during his 40-year career. “It will never be duplicated. There’s a lot of long-distance paddlers, but I don’t see anyone ever matching those records of Verlen’s. “He was obsessed.” Woodruff, an 86-year-old Michigan topology guru and Delta Township resident, is the mastermind behind the Ultimate Hugh Heward Challenge — an estimated 23-day trek beginning next Friday in Belle Isle and ending in Chicago.

His call has been answered by four Michigan men and one from Florida who plan to emulate the 1790 feat of British trader Hugh Heward as a tribute to Kruger’s accomplishments and love of paddling. Kruger, a former plumbing contractor, died of cancer in 2004 at age 82. He befriended Woodruff before Grand River Expedition ’90, a 260-mile trip down its length. “I think you have to be genetically inclined to do something like this,” said Jon Holmes, 43, a 15-year kayak instructor with Bill & Paul’s Sport-haus, 1200 E. Paris Ave. SE. “I don’t really know how well I’m going to stack up,” Holmes said. “I’ve dreamt of doing something along these lines, but I’ve never had the opportunity.”

Holmes has embarked on three-mile races and six-day trips, including one along the shoreline of Lake Superior Provincial Park, but now he’s preparing to tackle a vastly different adventure. To get in shape, he does situps, pushups and four-mile runs three days per week. He and business partner Rusty McBride began paddling upstream along the Grand from Ada to Lowell on Fridays.

Charles Parmelee has a good idea what he’s in for, having traveled an abbreviated version of the route in 2008. The 52-year-old Leslie man paddled 320 miles beginning at the mouth of the Huron in Belle Isle to Grand Haven. Parmelee, a retired General Motors toolmaker and past president of the Lansing Oar & Paddle Club, had to contend with snow and paddling upstream on the Huron River at its highest level in 40 years, he said. An overhanging branch dumped him into fast currents near Ann Arbor as he tried to retrieve a lost hat. Not again, he said. “If I lose my hat this time, it’s gone,” he said. Parmelee struggled to explain what draws him to such rugged endurance tests. He dropped 25 pounds during his last trip, he said. “Some people ask me why, and I don’t really have a real answer,” he said. “I got the gypsy blood, I guess. The only difference between me and a lot of people is I have the time.”

The route will take paddlers over two dozen portages, the longest of which is seven miles. Extra hands and wheeled canoe carts help trim the number of trips, Parmelee said. Legendary canoeist Verlen Kruger, who died in 2004, would have loved this 465-mile adventure, friends say. While he and others may grab a bite at a local restaurant, Holmes said he plans to filter water and otherwise pattern his trip after the way Kruger would do it. No one plans to bed down at a local motel, Parmelee said. The squad will find safe locales to camp along the route.

The Ultimate Hugh Heward Challenge is timed so participants can meet up with other paddlers for the 50-mile Hugh Heward Challenge down the Grand from Dimondale to Portland. That event, which drew more than 80 canoeing enthusiasts in 2008, is a fundraiser for the Verlen Kruger Memorial Board. The group plans to erect a life-size bronze statue honoring Kruger at the Thompson Field canoe landing in Portland. An unveiling date has not been set.